Cesium fluoride → HCID 66598070, compound

HRID 1483795Notes

Reaction equation

HRID 1483795 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C:5](=[O:16])[CH2:4]1.CCN(C(C)C)C(C)C.Cl[C:27]1[CH:28]=[CH:29][C:30]2[N:31]([C:33]([C:36]3[CH:41]=[CH:40][CH:39]=[C:38]([O:42][C:43]([F:46])([F:45])[F:44])[CH:37]=3)=[CH:34][N:35]=2)[N:32]=1.[F-].[Cs+]>CS(C)=O.O.C(Cl)Cl>[O:16]=[C:5]1[CH2:4][CH:3]([CH2:2][NH:1][C:27]2[CH:28]=[CH:29][C:30]3[N:31]([C:33]([C:36]4[CH:41]=[CH:40][CH:39]=[C:38]([O:42][C:43]([F:44])([F:46])[F:45])[CH:37]=4)=[CH:34][N:35]=3)[N:32]=2)[CH2:8][CH2:7][N:6]1[C:9]([O:11][C:12]([CH3:13])([CH3:15])[CH3:14])=[O:10]

Participants

8

Reactant 4

HCID 25953Cesium fluorideHCID 81531DiisopropylethylamineHCID 593798616-Chloro-3-(3-(trifluoromethoxy)phenyl)imidazo[1,2-b]pyridazineHCID 66598171HCID 66598171, compound

Product 1

HCID 66598070HCID 66598070, compoundYield 74.5%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of compound tert-butyl 4-(aminomethyl)-2-oxopiperidine-1-carboxylate (37 mg, 0.16 mmol), DIEA (0.6 mL, 3.5 mmol), 6-chloro-3-(3-(trifluoromethoxy)phenyl)imidazo[1,2-b]pyridazine (50 mg) and CsF (17 mg, 0.11 mmol) in DMSO (2 mL) was stirred at 120° C. overnight. The mixture was diluted with H2O (20 mL) and CH2Cl2 (20 mL). The organic phase was separated and condensed to give crude compound tert-butyl 2-oxo-4-(((3-(3-(trifluoromethoxy)phenyl)imidazo[1,2-b]pyridazin-6-yl)amino)methyl)piperidine-1-carboxylate (60 mg).

Workup

  1. customThe organic phase was separated
  2. customcondensed

Sources & evidence

ORD record
ord-ad9bbcde5d4b4a5ca2160ac17140153a
Source dataset
uspto-grants-2016_08
Patent number
US09416132B2

Reaction notes

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